CA2873793C - Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase - Google Patents

Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase Download PDF

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Publication number
CA2873793C
CA2873793C CA2873793A CA2873793A CA2873793C CA 2873793 C CA2873793 C CA 2873793C CA 2873793 A CA2873793 A CA 2873793A CA 2873793 A CA2873793 A CA 2873793A CA 2873793 C CA2873793 C CA 2873793C
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Prior art keywords
bcn
group
polypeptide
amino acid
tetrazine
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CA2873793A
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English (en)
French (fr)
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CA2873793A1 (en
Inventor
Jason Chin
Kathrin Lang
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United Kingdom Research and Innovation
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United Kingdom Research and Innovation
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Priority claimed from GBGB1208875.3A external-priority patent/GB201208875D0/en
Priority claimed from GBGB1210303.2A external-priority patent/GB201210303D0/en
Application filed by United Kingdom Research and Innovation filed Critical United Kingdom Research and Innovation
Publication of CA2873793A1 publication Critical patent/CA2873793A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/13—Labelling of peptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K2/00—Peptides of undefined number of amino acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/93—Ligases (6)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y601/00—Ligases forming carbon-oxygen bonds (6.1)
    • C12Y601/01—Ligases forming aminoacyl-tRNA and related compounds (6.1.1)
    • C12Y601/01026—Pyrrolysine-tRNAPyl ligase (6.1.1.26)
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • Biomedical Technology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Urology & Nephrology (AREA)
  • Cell Biology (AREA)
  • Food Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Peptides Or Proteins (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
CA2873793A 2012-05-18 2013-05-15 Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase Active CA2873793C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GBGB1208875.3A GB201208875D0 (en) 2012-05-18 2012-05-18 Methods
GB1208875.3 2012-05-18
GB1210303.2 2012-06-08
GBGB1210303.2A GB201210303D0 (en) 2012-06-08 2012-06-08 Polypeptides and methods
PCT/GB2013/051249 WO2013171485A1 (en) 2012-05-18 2013-05-15 Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase.

Publications (2)

Publication Number Publication Date
CA2873793A1 CA2873793A1 (en) 2013-11-21
CA2873793C true CA2873793C (en) 2022-02-22

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CA2873793A Active CA2873793C (en) 2012-05-18 2013-05-15 Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase

Country Status (8)

Country Link
US (3) US20150148525A1 (enExample)
EP (1) EP2852664B1 (enExample)
JP (1) JP6343604B2 (enExample)
CN (2) CN108410827B (enExample)
BR (1) BR112014028588B1 (enExample)
CA (1) CA2873793C (enExample)
IN (1) IN2014DN09922A (enExample)
WO (1) WO2013171485A1 (enExample)

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GB2528227A (en) 2014-03-14 2016-01-20 Medical Res Council Cyclopropene amino acids and methods
US12091391B2 (en) 2015-04-30 2024-09-17 Oregon State University Reagents and methods for bioorthogonal labeling of biomolecules in living cells
JP6967221B2 (ja) * 2015-08-19 2021-11-17 国立研究開発法人理化学研究所 非天然アミノ酸導入抗体
CN105254655B (zh) * 2015-11-20 2017-03-22 江汉大学 一种基于bodipy的荧光氨基酸及其合成方法与应用
CN106565762B (zh) * 2016-11-17 2018-10-23 陕西师范大学 一种原位产生近红外荧光的bodipy类染料及其制备和应用
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JOP20190245A1 (ar) 2017-04-20 2019-10-15 Novartis Ag أنظمة توصيل إطلاق مستدام تتضمن روابط بلا أثر لنقطة الربط
US11560384B2 (en) 2017-05-04 2023-01-24 University Of Utah Research Foundation Benzonorbornadiene derivatives and reactions thereof
AR111963A1 (es) * 2017-05-26 2019-09-04 Univ California Método y moléculas
TW202027794A (zh) 2018-10-03 2020-08-01 瑞士商諾華公司 血管生成素樣３多肽之持續遞送
GB201817444D0 (en) 2018-10-26 2018-12-12 Res & Innovation Uk Methods and compositions
CN111849929B (zh) * 2019-04-30 2021-05-11 苏州鲲鹏生物技术有限公司 高效引入赖氨酸衍生物的氨酰基—tRNA合成酶
GB201906775D0 (en) 2019-05-14 2019-06-26 Res & Innovation Uk Synthetic genome
IL267744A (en) * 2019-06-30 2019-08-29 Nat Inst Biotechnology Negev Ltd Labelling molecules and methods of use thereof
CN115701451B (zh) * 2021-08-02 2023-08-01 宁波鲲鹏生物科技有限公司 高效引入赖氨酸衍生物的氨酰基-tRNA合成酶及其应用
EP4399283A2 (en) * 2021-09-06 2024-07-17 Veraxa Biotech GmbH Novel aminoacyl-trna synthetase variants for genetic code expansion in eukaryotes
JP2026519275A (ja) 2023-04-28 2026-06-15 ユナイテッド キングダム リサーチ アンド イノベーション ｔＲＮＡに基づく方法及び関連組成物
GB202307998D0 (en) 2023-05-29 2023-07-12 Res & Innovation Uk Aminoacyl-irna synthetase sets
CN119613545B (zh) * 2024-12-16 2025-09-16 天津大学 非天然氨基酸修饰的抗ccl5纳米抗体

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Also Published As

Publication number Publication date
IN2014DN09922A (enExample) 2015-08-14
JP6343604B2 (ja) 2018-06-13
BR112014028588B1 (pt) 2023-03-21
EP2852664A1 (en) 2015-04-01
US20230340013A1 (en) 2023-10-26
US20150148525A1 (en) 2015-05-28
WO2013171485A1 (en) 2013-11-21
CA2873793A1 (en) 2013-11-21
CN108410827A (zh) 2018-08-17
EP2852664B1 (en) 2017-09-06
HK1208704A1 (en) 2016-03-11
US11732001B2 (en) 2023-08-22
BR112014028588A8 (pt) 2021-06-29
BR112014028588A2 (pt) 2017-06-27
CN108410827B (zh) 2023-05-09
JP2015523965A (ja) 2015-08-20
CN104718285A (zh) 2015-06-17
US20200271658A1 (en) 2020-08-27

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